Synthesis and Antimicrobial Activity of Novel Hydrazone and 1,2,4-Triazole-3-thione Derivatives

Yankin, A. M.; Nosova, N. V.; Новикова, В. В.; Гейн, В. Л.

doi:10.1134/s1070363222020050

Cited by 2 publications

(3 citation statements)

References 30 publications

(44 reference statements)

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“…1,2,4-triazole-3-thione (TZT) derivatives: TZT was identified as a potential motif that interacted with the two zinc ions of MBL (L1) through one of the three nitrogen atoms, and sulfur atom, at the same time. An initial crystal structure evaluation of the analogous compound in complex with the L1 enzyme [132] led to synthesis [133][134][135][136][137][138][139][140] (Scheme 36) and enzymatic inhibition studies on a variety of compounds with variable substituents at positions 4 and 5 of TZT. A number of selected compounds exhibited IC 50 values in the micro-molar range against representative MBLs (i.e., L1, VIM-4, VIM-2, NDM-1, and IMP-1 and CphA); however, limited success was observed in the microbiological assays [134][135][136][137]139,140].…”

Section: 24-triazole-3-thione (Tzt) Derivativesmentioning

confidence: 99%

Recent Developments to Cope the Antibacterial Resistance via β-Lactamase Inhibition

et al. 2022

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Antibacterial resistance towards the β-lactam (BL) drugs is now ubiquitous, and there is a major global health concern associated with the emergence of new β-lactamases (BLAs) as the primary cause of resistance. In addition to the development of new antibacterial drugs, β-lactamase inhibition is an alternative modality that can be implemented to tackle this resistance channel. This strategy has successfully revitalized the efficacy of a number of otherwise obsolete BLs since the discovery of the first β-lactamase inhibitor (BLI), clavulanic acid. Over the years, β-lactamase inhibition research has grown, leading to the introduction of new synthetic inhibitors, and a few are currently in clinical trials. Of note, the 1, 6-diazabicyclo [3,2,1]octan-7-one (DBO) scaffold gained the attention of researchers around the world, which finally culminated in the approval of two BLIs, avibactam and relebactam, which can successfully inhibit Ambler class A, C, and D β-lactamases. Boronic acids have shown promise in coping with Ambler class B β-lactamases in recent research, in addition to classes A, C, and D with the clinical use of vaborbactam. This review focuses on the further developments in the synthetic strategies using DBO as well as boronic acid derivatives. In addition, various other potential serine- and metallo- β-lactamases inhibitors that have been developed in last few years are discussed briefly as well. Furthermore, binding interactions of the representative inhibitors have been discussed based on the crystal structure data of inhibitor-enzyme complex, published in the literature.

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Section: 24-triazole-3-thione (Tzt) Derivativesmentioning

confidence: 99%

Recent Developments to Cope the Antibacterial Resistance via β-Lactamase Inhibition

et al. 2022

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“…They have shown promising potential in the development of antimicrobial and anticancer drugs. Numerous studies have demonstrated the potent antimicrobial activity of hydrazone‐based compounds against various bacterial and fungal pathogens [8–12] . Additionally, hydrazone derivatives have represented promising anticancer activity by inhibiting cancer cell proliferation and inducing apoptosis [13–19] .…”

Section: Introductionmentioning

confidence: 99%

“…Numerous studies have demonstrated the potent antimicrobial activity of hydrazone-based compounds against various bacterial and fungal pathogens. [8][9][10][11][12] Additionally, hydrazone derivatives have represented promising anticancer activity by inhibiting cancer cell proliferation and inducing apoptosis. [13][14][15][16][17][18][19] The mechanism of action of these compounds involves targeting specific cellular pathways and enzymes, facilitated by their multiple hydrogen bond acceptor/donor atoms that can interact with biological targets.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Novel Metacetamol Derivatives with Hydrazone Moiety as Anticancer and Antimicrobial Agents

Şenkardeş,

Atlıhan,

Çayır

et al. 2023

Chemistry & Biodiversity

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By exploiting the wide biological potential of the hydrazone scaffold, a series of hydrazone derivatives were synthesized, starting from N‐(3‐hydroxyphenyl)acetamide (metacetamol). The structures of the compounds were determined using IR, 1H and 13C‐NMR, and mass spectroscopic methods. The obtained molecules (3 a–j) were evaluated for their anticancer potential against MDA‐MB‐231 and MCF‐7 breast cancer cell lines. According to the CCK‐8 assay, all tested compounds showed moderate to potent anticancer activity. Among them, N‐(3‐(2‐(2‐(4‐nitrobenzylidene)hydrazinyl)‐2‐oxoethoxy)phenyl)acetamide (3 e) was found to be the most effective derivative with an IC50 value of 9.89 μM against MDA‐MB‐231 cell lines. This compound was further tested for its potential effects on the apoptotic pathway. Molecular docking studies was also carried out for 3 e in the colchicine binding pocket of tubulin. Additionally, compound 3 e also demonstrated effective antifungal activity, particularly against Candida krusei (MIC=8 μg/ml), indicating that nitro group at the 4th position of the phenyl ring was the most preferable substituent for both cytotoxic and antimicrobial activity. Our preliminary findings suggest that compound 3 e could be exploited as a leading structure for further anticancer and antifungal drug development.

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Synthesis and Antimicrobial Activity of Novel Hydrazone and 1,2,4-Triazole-3-thione Derivatives

Cited by 2 publications

References 30 publications

Recent Developments to Cope the Antibacterial Resistance via β-Lactamase Inhibition

Recent Developments to Cope the Antibacterial Resistance via β-Lactamase Inhibition

Synthesis and Evaluation of Novel Metacetamol Derivatives with Hydrazone Moiety as Anticancer and Antimicrobial Agents

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